Founder-CEO Enjoyment

A founder-CEO I coach recently asked me two questions no one has ever asked me before: “What do founder-CEOs actually enjoy about their job? And do their answers change when they are no longer building from 0 to 1, but from 1 to scale?”

I took maybe 10 seconds to skim through over a decade of coaching memories and distill some semblance of an answer. I finally told him: “Huh. Well, I would want to actually survey folks for a better answer, but my best guess right now is there are three things that they tend to enjoy in that 1 to scale period. 

First off, there is joy in bringing their product or service to the masses, moving their company from vision to fruition. Second, I bet a lot of people would talk about building their team; how they enjoy being able to hire more and more experienced teammates or executives and build a team that executes and is just fun to work with, to coach/help grow, etc. And then last, I’m thinking about external engagement, that many founder-CEOs once they’ve reached that point are enjoying being a thought leader in their space, whether that is speaking at conferences or with media or with larger and larger customers or through writing or influence in their space more broadly.” 

And then, feeling both self-unsatisfied and deeply curious, I decided to do that survey. I reached out to 38 founder-CEOs who I know personally through either coaching or T-groups. 

Here’s what happened: 

• I received responses from 22 founder-CEOs ranging from early stage to growth-stage and one that was post-exit 

• I asked them “what elements of your current founder-CEO role do you enjoy?” and then asked them to give me some data to help me understand their “stage” (revenue, funding round, headcount, etc) 

• I read and re-read their answers over again to organize their qualitative responses into themes and sub-themes that I could get my brain around. 

And here is what I found in my survey sample: 

1 - The most common sources of founder-CEO enjoyment are, in order: “The Team”; “Having an Impact”; Learning & Variety; Product; Winning; and Lifestyle Alignment

2 - There weren’t significant or obvious differences between the 0-to-1 stage and the 1-scale stage. If I had to stretch to report something, I could say that at 0-to-1 stage “bringing vision to fruition” was more commonly reported, while at 1-scale stage “lifestyle/life alignment” showed up more frequently.

Now, let’s dive into the details and share some illustrative quotes: 

“The Team” (18 of 22) 

Over 80% of respondents mentioned at least one thing related to their team as being an element of their current role that they enjoy, although the nature of how the team was generating enjoyment varied within this larger category.

Here were the sub-categories and distinctions I observed: 

“The Team I See”: 10 respondents framed their enjoyment of the team in a less active, but more intentional & integrated way. The team or culture is something that they have ostensibly created, but now they enjoy just being a part of it and they enjoy seeing it happen alongside, or even without, them. 

• “I really enjoy taking a moment on team calls to "snap out" of being on the team and just observe the fact that there are X number of people who all have different paths, with so much collective knowledge and aspirations, and potential. All of them working with each other at this point in time, giving each other energy, and having caring, supportive relationships. There's a real great sense of pride in creating a space where that can happen and being a part of it.”

• “Continuing to strengthen the culture while also observing how the culture has taken a life of its own over the years (and I like where it is).”

• “seeing the company run well while not being too involved always feels like success.” 
  

“The Team I Lead”: 9 respondents framed their enjoyment as more active with comments referencing “running” or “leading” a team that is high-performing

• “Spending time with my team & being a leader for them, fostering an environment where people feel proud to work and motivated by what we are trying to achieve”

• “I love the feeling of being responsible for a group of humans…I love creating and providing work environments that good people thrive in. I love the opportunity to prove that high performance and heart can go hand in hand.”

Talent: 4 mentioned smart or talented teammates explicitly.

• “Collaborating with really talented people”

• “I love to interact with smarter people than I am.”

Growth: 4 reported enjoyment of coaching/mentoring and helping their teammates to grow

• “Seeing people I have worked with for some time grow and become better people. Continuing to provide value to them or see them onto their next challenge knowing we are parting ways and they are stronger than before.”

• “Career discussions with execs or other talented individuals”
  

Opportunities: And 2 referenced the opportunities (professional and financial) their company was able to create for their teammates 

• “Having more options to help high performers grow. Since we had such a small team for so long, there weren’t as many options to give someone new opportunities as there are now”

“Having An Impact” (9 of 22)

The next most common reported source of enjoyment is a category that includes mentions of customer impact and the enjoyment of solving problems. In this category, I also included comments that referenced “fruition” or the experience of moving from a vision to reality.

• “Creating a product that people love and has a big impact on the world! We got 1M people using our product last year!!!!”

• “I love the freedom of creating and executing strategy to solve real life problems of the world.” 

• “I love seeing things come alive in the "real" world. e.g. moving into a new office which we got to decorate with tons of cool stuff (photos of customers using our product, etc.), seeing customers use our product, seeing people react to us online, etc. This isn't an ego thing - I don't need my name out there. It's seeing something you made from literally nothing get traction and have an ‘impact’ on the world.”

Learning & Variety (7 of 22) 

Almost ⅓ of respondents mentioned enjoying how their role enables them to learn and experience a variety of challenges both day-to-day and over a longer-term. 

• “Learning as the company evolves, though the different stages”

• “I love having my fingers in many areas and not just one specific area...I enjoy never having the same day twice.”

• “Constantly learning and getting pushed…The fact that I'm never ever bored”

• “I also love the challenge of learning how to hold more and more complexity, and to try to do so with grace.”

• “Scaling myself as we scale.”

Product (6 of 22)

Many founder-CEOs double as product leaders during early-stage, and they often carry forward their passion, conviction and curiosity about product into later stages as their companies scale. I heard respondents tell me they enjoy:

• “Brainstorming about new product ideas, working with engineers and designers to explore new innovations”

• “the creativity around product - creating lots of information // generating lots of ideas (user interviews, hypotheses, recorded user sessions, etc) and then connecting those dots and finding the simplest way to solve the problem for the user”

• “the product discovery and design process- this has always been my favorite part and that hasn’t changed”

• “conceiving + collaborating on product features”

Winning (5 of 22) 

Founder-CEOs also reported enjoyment when they can experience success, clear wins and a sense of accomplishment.

• “Success. When the company wins a big deal, closes a round…”

• “hitting audacious goals”

• “when we win deals together”

• “I like big "moments": closing a round of funding, a new offer letter getting signed, hitting a new milestone, etc. So much of the day to day isn't very concrete, it's nice when you can finish a specific thing and enjoy it.”

Lifestyle Alignment (4 of 22) 

I hesitated at first to include this category because I don’t think anyone would claim that the Founder-CEO lifestyle, in general, is an enviable one. Venture-backed businesses and lifestyle businesses, are fundamentally different in their aims. Founders can spend years in early stage somewhere between “all-consuming” and “unrelenting grind”, but maybe having such a visceral sense of comparison is what enables them to report enjoying the relative degree of lifestyle alignment some can experience at growth stage. This was the smallest of the categories, but I included it because it is an interesting data point — the same role that required an all-consuming commitment years ago might evolve into a role where you have the power, resources and leverage to reset your own work-life boundaries in a way that’s more aligned with what you want.

• “the life stage alignment between my company and my own life is a huge plus!”

• “Flexible schedule so I can spend time with the kids.” 

• “Working on my own terms”

Other

I do want to note that there were 10 responses across 6 respondents that simply didn’t fit into my categories, but also weren’t repeated enough by others to merit creating a category. The comments touched on a wide range of experiences including: Customer Interactions; Getting To Put/See My Values In Action; Specific Functional Leadership Roles; and Moving from Product to Platform. 

Surprises

As I read (and re-read and re-read) the responses, there were 4 things that stood out to me: 

1 - “Teaminess” - At first, I was surprised by the sheer “teaminess” of so many of the responses. While I initially had guessed that Team-Building would be in the mix, but I didn’t expect it to be so common. I initially discounted this result by chalking it up to potential bias in my sample set. All 22 of the respondents are current/former coaching clients or alumni of T-groups (or both!) The type of founder-CEO who elects to work with an interpersonal dynamics nerd-coach like me or who signs up to participate in a T-group must have some predisposition towards Teaminess, right? On the other hand, social psychologists repeatedly find that relationships and sense of connection is a fundamental driver of human happiness and well-being. So, maybe this result should be blazingly obvious?

2 - External-Facing Thought Leadership, Anyone? - Only one respondent mentioned anything about thought-leadership and external presence (“public speaking opps in our space”). This one truly shocked me. Did you all learn post-pandemic that you don’t actually like speaking at conferences? Is talking with the media something you “have” to do vs. something you “get” to do? Is it that you could write a thoughtful blog post about a trend in your space, but your content team hasn’t flagged that as a key priority this quarter? Or, as I reflected more, maybe this is something more founder-CEOs would enjoy, but either (1) you don’t feel you can choose that right now or (2) you’ve intentionally shifted your energy and attention inside your company (“I’m focused on product roadmap and leveling up the exec team this year”) or into other areas of your lives. (i.e., “I’d rather be home with my family than fly to London for that event.”) 

3 - Strategy - Only 3 respondents explicitly referenced the word “strategy” in their responses. This surprised me a bit at first. I’ve heard many founder-CEOs sum up their jobs to me as: Strategy, People & Financing. I found myself wondering if strategy is now more a tool CEOs use or an integrated way of thinking across everything you do vs. something you recognize as a standalone element of the role on its own. 

4 - Product Joy After Series B - I’ve heard tales of woe about how product-minded CEOs often lose their mojo as the company scales and they get further and further removed from Product. So, I was pleasantly surprised and encouraged to see post Series B stage CEOs reporting product innovation and their high-level involvement in Product as a source of enjoyment for them.

Self-Coaching: So, what might you try next?

Reflect: First and most simply, what thoughts and feelings come up for you as you read through this? Are you feeling validated/seen or more disconnected? Are you feeling envious that other founder-CEOs are experiencing joy and you’re not? Are you feeling motivated to increase the time & energy you spend in certain elements of your role? 

Write: If you’re feeling motivated or curious to re-examine or make some changes to your role, you can experiment with my Write your Own Job Description exercise and modify the instructions to review your current role for enjoyment and design a future role that has the potential to increase your daily enjoyment. (And if you start to realize you may no longer want the CEO job at your company read this )

Track: One of the founder-CEOs in the survey shared an exercise she did for herself and now plans to replicate with her executive team. She created a 2x2 matrix where one axis was “Fun For Me” | “Not Fun For Me” and the other axis was “Important for Company” | “Not Important For Company.” She then kept track of how she was spending her time over 6 weeks and filled out the 2x2 with her various responsibilities and activities. Her next step, once the exec team has done their own analysis, is to set a goal for each individual to spend as much of their time as possible in the Fun For Me+Important To Company box and to explore opportunities to delegate more and/or shift responsibilities to other members of the exec team who might enjoy those activities more.

Re-frame: To be clear, there is a LOT of non-enjoyment in the daily reality of a founder-CEO, regardless of stage. If there were no pain, struggle, anxiety, loneliness, disappointment, disenchantment, stress, then I would not have my job of helping founder-CEOs navigate all the emotional downs in between the ups. 

And yet, I was struck by how much my own mood elevated just in reading the 22 responses. There is clearly pleasure, joy, meaning, fulfillment in these roles as well. 

If you can allow both emotional experiences to co-exist, and not force them to cancel out, you can slow down a bit to savor what there is to enjoy in this role in this season of your life. 

The respondent in the survey who is post-exit, perhaps, put it best: 

“Since I sold my company 2.5 years ago, I'm no longer really a founder/CEO... I'm currently the CMO of the acquiring business. I miss the CEO/founder role and don't get the same satisfaction from the current job…I really shouldn't complain. The job is flexible, I believe I'm making an impact, my boss is good to work for, my coworkers are friendly and supportive, and I'm in an industry I love. I just miss the CEO role.”

You might miss this someday. 

Photo by Jay-Pee Peña 🇵🇭 on Unsplash